US9150575B2 - Piperidinylpyrazolopyridine derivative - Google Patents

Piperidinylpyrazolopyridine derivative Download PDF

Info

Publication number
US9150575B2
US9150575B2 US14/566,460 US201414566460A US9150575B2 US 9150575 B2 US9150575 B2 US 9150575B2 US 201414566460 A US201414566460 A US 201414566460A US 9150575 B2 US9150575 B2 US 9150575B2
Authority
US
United States
Prior art keywords
group
trifluoromethyl
pyridin
piperidin
pyrazolo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US14/566,460
Other languages
English (en)
Other versions
US20150152102A1 (en
Inventor
Hideki Kobayashi
Nobuyuki Ohkawa
Daisuke Takano
Hideki Kubota
Toshio Onoda
Toshio Kaneko
Masami Arai
Naoki Terasaka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daiichi Sankyo Co Ltd
Original Assignee
Daiichi Sankyo Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daiichi Sankyo Co Ltd filed Critical Daiichi Sankyo Co Ltd
Assigned to DAIICHI SANKYO COMPANY, LIMITED reassignment DAIICHI SANKYO COMPANY, LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ARAI, MASAMI, TAKANO, DAISUKE, KANEKO, TOSHIO, KOBAYASHI, HIDEKI, KUBOTA, HIDEKI, OHKAWA, NOBUYUKI, ONODA, Toshio, TERASAKA, NAOKI
Publication of US20150152102A1 publication Critical patent/US20150152102A1/en
Application granted granted Critical
Publication of US9150575B2 publication Critical patent/US9150575B2/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4875—Compounds of unknown constitution, e.g. material from plants or animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
US14/566,460 2012-06-14 2014-12-10 Piperidinylpyrazolopyridine derivative Expired - Fee Related US9150575B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2012134431 2012-06-14
JP2012-134431 2012-06-14
PCT/JP2013/066306 WO2013187462A1 (ja) 2012-06-14 2013-06-13 ピペリジニルピラゾロピリジン誘導体

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2013/066306 Continuation WO2013187462A1 (ja) 2012-06-14 2013-06-13 ピペリジニルピラゾロピリジン誘導体

Publications (2)

Publication Number Publication Date
US20150152102A1 US20150152102A1 (en) 2015-06-04
US9150575B2 true US9150575B2 (en) 2015-10-06

Family

ID=49758280

Family Applications (1)

Application Number Title Priority Date Filing Date
US14/566,460 Expired - Fee Related US9150575B2 (en) 2012-06-14 2014-12-10 Piperidinylpyrazolopyridine derivative

Country Status (13)

Country Link
US (1) US9150575B2 (de)
EP (1) EP2862861B1 (de)
JP (1) JPWO2013187462A1 (de)
KR (1) KR20150021036A (de)
CN (1) CN104781257A (de)
BR (1) BR112014030954A2 (de)
CA (1) CA2876382A1 (de)
ES (1) ES2563861T3 (de)
HK (1) HK1207375A1 (de)
IN (1) IN2014MN02512A (de)
RU (1) RU2015100942A (de)
TW (1) TW201402572A (de)
WO (1) WO2013187462A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160376267A1 (en) * 2013-12-13 2016-12-29 Daiichi Sankyo Company, Limited 5-hydroxy-4-(trifluoromethyl)pyrazolopyridine derivative
US10138240B2 (en) 2015-06-11 2018-11-27 Daiichi Sankyo Company, Limited Crystal of 5-hydroxy-4-(trifluoromethyl)pyrazolopyridine derivative

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108354933A (zh) 2013-03-15 2018-08-03 维颂公司 作为丝氨酸蛋白酶抑制剂的多取代芳族化合物的制药用途
WO2015050148A1 (ja) * 2013-10-04 2015-04-09 第一三共株式会社 ３－アリールピラゾロピリジン誘導体
WO2015076353A1 (ja) * 2013-11-25 2015-05-28 第一三共株式会社 ３－アルキルピラゾロピリジン誘導体
WO2015087995A1 (ja) * 2013-12-13 2015-06-18 第一三共株式会社 シクロアルキル又はヘテロシクリルピラゾロピリジン誘導体
WO2015087996A1 (ja) * 2013-12-13 2015-06-18 第一三共株式会社 イミダゾピリジン誘導体
CN103694220A (zh) * 2013-12-30 2014-04-02 张磊 新型吡唑-3-甲酸酯及合成方法
WO2015111545A1 (ja) * 2014-01-21 2015-07-30 第一三共株式会社 縮合ピラゾール誘導体
CA2960790A1 (en) 2014-09-17 2016-03-24 Verseon Corporation Pyrazolyl-substituted pyridone compounds as serine protease inhibitors
LT3261639T (lt) 2015-02-27 2022-11-25 Verseon International Corporation Pakaitiniai pirazolo junginiai kaip serino proteazės inhibitoriai
CN106916143B (zh) * 2017-03-14 2019-09-27 哈尔滨医科大学 一种预防和治疗冠心病的药物及其应用
WO2019189046A1 (ja) 2018-03-30 2019-10-03 第一三共株式会社 Ｌｃａｔ欠損症治療薬
WO2021207308A1 (en) * 2020-04-09 2021-10-14 Disarm Therapeutics, Inc. Condensed pyrazole derivatives as inhibitors of sarm1

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008002591A2 (en) 2006-06-26 2008-01-03 Amgen Inc Methods for treating atherosclerosis
WO2012028243A1 (en) 2010-09-02 2012-03-08 Merck Patent Gmbh Pyrazolopyridinone derivatives as lpa receptor antagonists

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005019200A2 (en) 2003-08-14 2005-03-03 Icos Corporation Aryl piperidine derivatives as vla-1 integrin antagonists and uses thereof
AU2005237500A1 (en) 2004-04-28 2005-11-10 Merck Sharp & Dohme Corp. 3,3-disubstituted tetrahydropyranyl cyclopentyl amide modulators of chemokine receptor activity
SE0403171D0 (sv) 2004-12-23 2004-12-23 Astrazeneca Ab New compounds
WO2007111323A1 (ja) 2006-03-27 2007-10-04 Toray Industries, Inc. ウレイド誘導体およびその医薬用途
DK2125794T3 (da) 2006-12-21 2011-01-24 Lilly Co Eli Imidazolidinonylaminopyrimidin-forbindelser til behandling af cancer
CA2684037C (en) 2007-04-11 2016-02-16 Canbas Co., Ltd. Compounds with anti-cancer activity
EP2205596A1 (de) 2007-09-24 2010-07-14 Comentis, Inc. (3-hydroxy-4-aminobutan-2-yl)-3-(2-thiazol-2-ylpyrrolidin-1-carbonyl)benzamidderivate und verwandte verbindungen als beta-secretase-inhibitoren zur behandlung
EP2080758A3 (de) 2007-11-29 2009-08-26 Bayer CropScience AG Halogen substituierte delta-1-Pyrroline
AU2008341953B2 (en) 2007-12-26 2013-05-02 Msd K.K. Sulfonyl substituted 6-membered ring derivative
RU2010143600A (ru) 2008-03-26 2012-05-10 Дайити Санкио Компани, Лимитед (Jp) Производное гидроксихиноксалинкарбоксамида
GB0903493D0 (en) 2009-02-27 2009-04-08 Vantia Ltd New compounds
US8394834B2 (en) 2009-08-25 2013-03-12 Hoffman-La Roche Inc. Pyrrolidines as NK3 receptor antagonists
AU2010300925A1 (en) 2009-09-30 2012-03-29 Merck Sharp & Dohme Corp. Novel compounds that are ERK inhibitors
FR2951172B1 (fr) 2009-10-13 2014-09-26 Pf Medicament Derives pyrazolopyridines en tant qu'agent anticancereux
JP2013532185A (ja) 2010-07-12 2013-08-15 ファイザー・リミテッド 化合物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008002591A2 (en) 2006-06-26 2008-01-03 Amgen Inc Methods for treating atherosclerosis
WO2012028243A1 (en) 2010-09-02 2012-03-08 Merck Patent Gmbh Pyrazolopyridinone derivatives as lpa receptor antagonists

Non-Patent Citations (9)

* Cited by examiner, † Cited by third party
Title
Badimon, J.J., et al., "Regression of Atherosclerotic Lesions by High Density Lipoprotein Plasma Fraction in the Cholesterol-Fed Rabbit," Journal of Clinical Investigation 85(4):1234-1241, Apr. 1990.
Balicki, R., "Studies in the Field of Nitrogen Heterocyclic Compounds. Part XI. Abnormal Cyclocondensation of Ethyl 4,4,4-Trifluoroacetoacetate With Aminopyrazoles," Polish Journal of Chemistry 57:789-797, 1983.
International Preliminary Report on Patentability mailed Dec. 16, 2014, issued in corresponding International Application No. PCT/JP2013/066306, filed Jun. 13, 2013, 6 pages.
International Search Report mailed Sep. 10, 2013, issued in corresponding International Application No. PCT/JP2013/066306, filed Jun. 13, 2013, 3 pages.
Iwata, A., et al., "Antiatherogenic Effects of Newly Developed Apolipoprotein A-I Mimetic Peptide/Phospholipid Complexes Against Aortic Plaque Burden in Watanabe-Heritable Hyperlipidemic Rabbits," Atherosclerosis 218(2):300-307, Oct. 2011.
Matsuura, F., et al., "HDL From CETP-Deficient Subjects Shows Enhanced Ability to Promote Cholesterol Efflux From Macrophages in an apoE- and ABCG1-Dependent Pathway," Journal of Clinical Investigation 116(5):1435-1442, May 2006.
Ross, R., "Cell Biology of Atherosclerosis," Annual Review of Physiology 57:791-804, 1995.
Steinberg, D., "Low Density Lipoprotein Oxidation and Its Pathobiological Significance," Journal of Biological Chemistry 272(34):20963-20966, Aug. 1997.
Yvan-Charvet, L., et al., "Inhibition of Cholesteryl Ester Transfer Protein by Torcetrapib Modestly Increases Macrophage Cholesterol Efflux to HDL," Arteriosclerosis, Thrombosis, and Vascular Biology 27(5):1132-1138, May 2007.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160376267A1 (en) * 2013-12-13 2016-12-29 Daiichi Sankyo Company, Limited 5-hydroxy-4-(trifluoromethyl)pyrazolopyridine derivative
US9796709B2 (en) * 2013-12-13 2017-10-24 Daiichi Sankyo Company, Limited 5-hydroxy-4-(trifluoromethyl)pyrazolopyridine derivative
US10138240B2 (en) 2015-06-11 2018-11-27 Daiichi Sankyo Company, Limited Crystal of 5-hydroxy-4-(trifluoromethyl)pyrazolopyridine derivative

Also Published As

Publication number Publication date
RU2015100942A (ru) 2016-08-10
EP2862861B1 (de) 2016-01-06
EP2862861A4 (de) 2015-04-22
HK1207375A1 (en) 2016-01-29
KR20150021036A (ko) 2015-02-27
JPWO2013187462A1 (ja) 2016-02-08
CA2876382A1 (en) 2013-12-19
US20150152102A1 (en) 2015-06-04
ES2563861T3 (es) 2016-03-16
EP2862861A1 (de) 2015-04-22
BR112014030954A2 (pt) 2017-06-27
WO2013187462A1 (ja) 2013-12-19
TW201402572A (zh) 2014-01-16
IN2014MN02512A (de) 2015-07-17
CN104781257A (zh) 2015-07-15

Similar Documents

Publication Publication Date Title
US9150575B2 (en) Piperidinylpyrazolopyridine derivative
CN112707893B (zh) 作为usp30抑制剂的1-氰基吡咯烷化合物
US9796709B2 (en) 5-hydroxy-4-(trifluoromethyl)pyrazolopyridine derivative
JP5301456B2 (ja) ヘテロアリールオキシキナゾリン誘導体
US20140051676A1 (en) Triazine-oxadiazoles
BR102015024618A2 (pt) compostos inibidores de quinase de ligação de tank
US20220079928A1 (en) Lysophosphatidic acid receptor antagonist and preparation method therefor
US20230092892A1 (en) Amino quinazoline derivatives as p2x3 inhibitors
US9751861B2 (en) N1-(3,3,3-trifluoro-2-hydroxo-2-methylpropionyl)-piperidine derivatives as inhibitors of pyruvate dehydrogenase kinase
JP2011136942A (ja) 新規な置換ピリミジン誘導体およびこれを含有する医薬
WO2015087996A1 (ja) イミダゾピリジン誘導体
KR102528255B1 (ko) 디아실글리세롤 아실트랜스퍼라제 2 억제제로서 유용한 신규 아미노 아릴 유도체 및 이의 용도
JP2015113323A (ja) ピペリジニルピラゾロピリジン誘導体の結晶
WO2015111545A1 (ja) 縮合ピラゾール誘導体
JP2007022937A (ja) ヘテロ環置換ベンズイミダゾール誘導体
WO2015050148A1 (ja) ３－アリールピラゾロピリジン誘導体

Legal Events

Date Code Title Description
AS Assignment

Owner name: DAIICHI SANKYO COMPANY, LIMITED, JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KOBAYASHI, HIDEKI;OHKAWA, NOBUYUKI;TAKANO, DAISUKE;AND OTHERS;SIGNING DATES FROM 20141112 TO 20141113;REEL/FRAME:034508/0359

STCF Information on status: patent grant

Free format text: PATENTED CASE

MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M1551); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Year of fee payment: 4

FEPP Fee payment procedure

Free format text: MAINTENANCE FEE REMINDER MAILED (ORIGINAL EVENT CODE: REM.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

LAPS Lapse for failure to pay maintenance fees

Free format text: PATENT EXPIRED FOR FAILURE TO PAY MAINTENANCE FEES (ORIGINAL EVENT CODE: EXP.); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

FP Lapsed due to failure to pay maintenance fee

Effective date: 20231006